Bailey's Billion$ (2005)

Sweet and savvy talking golden retriever, Bailey (Jon Lovitz), is one doggone lucky pooch when his devoted owner, Constance Pennington (Jackie Burroughs), leaves him her entire billion-dollar fortune. Bailey is lucky, that is, until he becomes the target of an elaborately-designed dognap scheme hatched by Constance's nasty nephew Caspar (Tim Curry) and his money-hungry wife Dolores (Jennifer Tilly). The despicable duo's wicked plan is to ultimately gain custody of the canine so they can get their greedy paws on his inheritance. Unfortunately for them, there's a thing or two they don't know about Bailey. Not only does he have great street smarts, he has great pals too. Bailey's loyal guardian Theodore Maxwell (Dean Cain), kind-hearted animal advocate Marge Maggs (Laurie Holden), her daughter Samantha (Angela Vallee), and a clever border collie named Tessa (Melissa DiMarco) set out on a hilarious madcap adventure to free their four-legged friend and put the nasty dognappers out of business for good.